US5240499A - Surfactant triazine compounds and their use - Google Patents
Surfactant triazine compounds and their use Download PDFInfo
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- US5240499A US5240499A US07/808,520 US80852091A US5240499A US 5240499 A US5240499 A US 5240499A US 80852091 A US80852091 A US 80852091A US 5240499 A US5240499 A US 5240499A
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- 239000004094 surface-active agent Substances 0.000 title abstract description 11
- 150000003918 triazines Chemical class 0.000 title abstract description 10
- 239000000049 pigment Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- -1 triazine compound Chemical class 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- 239000000126 substance Substances 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
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- 239000000543 intermediate Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000000485 pigmenting effect Effects 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
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- 239000004814 polyurethane Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- WGOUYMLKXVOCHM-UHFFFAOYSA-N NCCCN.Cl.Cl.Cl Chemical compound NCCCN.Cl.Cl.Cl WGOUYMLKXVOCHM-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 238000001595 flow curve Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- ULDIVZQLPBUHAG-UHFFFAOYSA-N n',n',2,2-tetramethylpropane-1,3-diamine Chemical compound CN(C)CC(C)(C)CN ULDIVZQLPBUHAG-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- KGBYOAZCHAMTID-UHFFFAOYSA-N n'-benzyl-n'-methylmethanediamine Chemical compound NCN(C)CC1=CC=CC=C1 KGBYOAZCHAMTID-UHFFFAOYSA-N 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/04—Sulfonates or sulfuric acid ester salts derived from polyhydric alcohols or amino alcohols or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paints Or Removers (AREA)
- Colloid Chemistry (AREA)
- Detergent Compositions (AREA)
Abstract
Description
__________________________________________________________________________ No. X Y.sup.1, Y.sup.2 each Z m __________________________________________________________________________ 3 --NH--(CH.sub.2).sub.3 --N(C.sub.2 H.sub.5).sub.2 --NH--C.sub.6 H.sub.4 --SO.sub.3 H --NH--C.sub.6 H.sub.4 --NH-- 2 4 --NH--(CH.sub.2).sub.3 --N(C.sub.2 H.sub.5).sub.2 --NH--C.sub.6 H.sub.4 --SO.sub.3 H --NH--C.sub.6 H.sub.4 --NH-- 5 5 --NH--(CH.sub.2).sub.3 --CH(CH.sub.3)N(C.sub.2 H.sub.5).sub.2 --NH--CH.sub.2 CH.sub.2 --SO.sub.3 H --NH--C.sub.6 H.sub.4 --NH-- 5 6 --NH--(CH.sub.2).sub.3 --N(C.sub.2 H.sub.5).sub.2 --NH--CH.sub.2 --CH.sub.2 --SO.sub.3 H --NH--C.sub.6 H.sub.4 --NH-- 2 7 --NH--(CH.sub.2).sub.3 --N(C.sub.2 H.sub.5).sub.2 --NH--CH.sub.2 --CH.sub.2 --SO.sub.3 H --NH--C.sub.6 H.sub.4 --NH-- 2 8 -- NH--(CH.sub.2).sub.3 -imidazolyl --NH--C.sub.6 H.sub.4 --COOH --NH--C.sub.6 H.sub.4 --NH-- 2 __________________________________________________________________________
__________________________________________________________________________ Amounts of educts: (p = parts) Stirred vessel (A) Stirred vessel (A) Stirred vessel (B) Stirred vessel (B) No. at 0 to 5° C. at 40° C. at 0 to 5° C. at 40° C. at 80° C. __________________________________________________________________________ 3 18.5 p. of cyanuric 13.0 p. of diethyl- 18.5 p. of cyanuric 5.4 p. of p-phenyl- 10.8 p. of p- chloride aminopropylamine chloride enediamine phenylenediamine 17.3 p. of sulfa- 17.3 p. of sulfa- nilic acid nilic acid 4 11.1 p. of cyanuric 7.8 p. of diethyl- 27.7 p. of cyanuric 6.5 p. of p-phenyl- 13.0 p. of p- chloride aminopropylamine chloride enediamine phenylenediamine 10.4 p. of sulfa- 26.0 p. of sulfa- nilic acid nilic acid 5 18.5 p. of cyanuric 15.8 p. of N,N-di- 46.1 p. of cyanuric 21.6 p. of p- 10.8 p. of p- chloride ethylamino-4- chloride phenylenediamine phenylenediamine 12.5 p. of taurine aminopentane 31.3 p. of taurine 6 20.3 p. of cyanuric 13.0 p. of diethyl- 20.3 p. of cyanuric 5.4 p. of p-phenyl- 10.8 p. of p- chloride aminopropylamine chloride enediamine phenylenediamine 12.5 p. of taurine 12.5 p. of taurine 7 18.5 p. of cyanuric 13.0 p. of diethyl- 18.5 p. of cyanuric 9.4 p. of 2,5-di- 18.8 p. of di- chloride aminopropylamine chloride aminobenzene- aminobenzene- 12.5 p. of taurine 12.5 p. of taurine sulfonic acid sulfonic acid 8 18.5 p. of cyanuric 12.5 p. of N-(3- 18.5 p. of cyanuric 5.4 p. of p- 10.8 p. of p- chloride aminopropyl)- chloride phenylenediamine phenylenediamine 13.7 p. of p-amino- imidazole 13.7 p. of p-amino- benzoic acid benzoic acid __________________________________________________________________________
__________________________________________________________________________ Exam- ple IR (KBr, cm.sup.-1) __________________________________________________________________________ 3 3400, 3000, 1630, 1590, 1550, 1500, 1410, 1220, 1160, 1030, 1000 4 3400, 3000, 1630, 1590, 1550, 1490, 1410, 1220, 1160, 1030, 1000 5 3300, 3000, 1630, 1600, 1560, 1500, 1410, 1210, 1160, 1030, 6 3300, 3000, 1570, 1500, 1420, 1210, 1160, 1030, __________________________________________________________________________
______________________________________ FS 3% P 1:10 TiO.sub.2 50:50 Met Visc(s) ______________________________________ Comparison -- -- -- 2.5 Example E very little significantly distinctly 1.0 more trans- more intense more intense parent ______________________________________
______________________________________ FS 3% P 1:10 TiO.sub.2 50:50 Met Gloss ______________________________________ Comparison -- -- -- 15 Example F identical significantly significantly 56 transparency more intense more intense ______________________________________
__________________________________________________________________________ FS 3% P 1:10 TiO.sub.2 50:50 Met Gloss __________________________________________________________________________ Pigment with additive -- -- -- 22 according to U.S. significantly significantly significantly Pat. No. 4,314,001 more transparent more intense more intense 61 Example J FS 3% P 1:10 TiO.sub.2 50:50 Met Pigment accord- -- -- -- ing to U.S. significantly distinctly distinctly Pat. No. 4,496,731 more transparent more intense more intense (Example 5) FS 3% P 1:10 TiO.sub.2 50:50 Met Example J Pigment accord- -- -- -- ing to U.S. distinctly markedly very little Pat. No. 4,189,582 more transparent more intense more intense (Example 2) Example J __________________________________________________________________________
__________________________________________________________________________ FS 3% P 1:10 TiO.sub.2 50:50 Met Visc(s) Gloss __________________________________________________________________________ Comparison -- -- -- 3.5 30 Example K significantly considerably considerably 4.9 71 more transparent more intense more intense FS 3% P 1:10 TiO.sub.2 50:50 Met Visc(s) Gloss Pigment accord- -- -- -- 8.9 30 ing to U.S. distinctly considerably significantly 4.9 71 Pat. No. 4,253,839 more transparent more intense more intense Example K __________________________________________________________________________ ##STR1##
Claims (5)
--A.sup.1 --D.sup.1 --NR.sup.1 R.sup.2 IVa
--A.sup.3 --D.sup.2 --E.sup.1 IVc
--A.sup.4 --Z*--A.sup.4 -- IVd
--NH--C.sub.6 H.sub.4 --A.sup.5 --C.sub.6 H.sub.4 --NH-- IVe
--NH--C.sub.2 --C.sub.3 -alkylene--A.sup.5 --C.sub.2 --C.sub.3 -alkylene--NH -- IFV
--A.sup.1 --D.sup.1 --NR.sup.1 R.sup.2 IVa
--A.sup.3 --D.sup.2 --E.sup.1 IVc
--A.sup.4 --Z*--A.sup.4 -- IVd
A.sup.3 --D.sup.2 --E.sup.1 IVh
--C.sub.2 --C.sub.3 -alkylene-Z**--C.sub.2 --C.sub.3 -alkylene IVi
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4041215 | 1990-12-21 | ||
DE4041215 | 1990-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
US5240499A true US5240499A (en) | 1993-08-31 |
Family
ID=6421059
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/808,520 Expired - Lifetime US5240499A (en) | 1990-12-21 | 1991-12-13 | Surfactant triazine compounds and their use |
Country Status (8)
Country | Link |
---|---|
US (1) | US5240499A (en) |
EP (1) | EP0492501B1 (en) |
JP (1) | JP3121412B2 (en) |
KR (1) | KR920012058A (en) |
CA (1) | CA2058274A1 (en) |
DE (1) | DE59108367D1 (en) |
DK (1) | DK0492501T3 (en) |
ES (1) | ES2096615T3 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040091896A1 (en) * | 2001-01-31 | 2004-05-13 | Hall Elizabeth Anne Howlet | Polymers |
CN101343254B (en) * | 2008-07-09 | 2010-06-09 | 中北大学 | Gemini surfactant containing triazine ring |
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US8845086B2 (en) | 2010-05-14 | 2014-09-30 | Fujifilm Imaging Colorants Limited | Printing process, polymer and ink |
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US9068092B2 (en) | 2011-07-07 | 2015-06-30 | Fujifilm Imaging Colorants Limited | Process for preparing polymers, polymers, dispersions, inks and uses |
US9434808B2 (en) | 2011-07-07 | 2016-09-06 | Fujifilm Imaging Colorants Limited | Process for preparing polymers, polymers, dispersions, inks and uses |
CN107754721A (en) * | 2017-10-12 | 2018-03-06 | 贺州学院 | Stilbene disulfonic acid natrium surfactant and its synthetic method and application |
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JPH07224162A (en) * | 1994-02-14 | 1995-08-22 | Hoechst Japan Ltd | Triazine polymer |
JP5880044B2 (en) * | 2009-05-07 | 2016-03-08 | 日産化学工業株式会社 | Carbon nanotube dispersion and solubilizer |
JP6274343B1 (en) * | 2017-05-12 | 2018-02-07 | 東洋インキScホールディングス株式会社 | Dispersant, dispersion composition, battery dispersion composition, electrode, battery |
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US20040091896A1 (en) * | 2001-01-31 | 2004-05-13 | Hall Elizabeth Anne Howlet | Polymers |
US7022808B2 (en) * | 2001-01-31 | 2006-04-04 | The Secretary Of State For Defence Dstl | Polymers |
US20060122289A1 (en) * | 2001-01-31 | 2006-06-08 | Hall Elizabeth A H | Polymers |
CN101343254B (en) * | 2008-07-09 | 2010-06-09 | 中北大学 | Gemini surfactant containing triazine ring |
CN101618300B (en) * | 2009-08-05 | 2011-12-07 | 中北大学 | Trimerization anion surface active agent |
US8845086B2 (en) | 2010-05-14 | 2014-09-30 | Fujifilm Imaging Colorants Limited | Printing process, polymer and ink |
US8927624B2 (en) | 2010-05-14 | 2015-01-06 | Fujifilm Imaging Colorants Limited | Dispersion, process for preparing a dispersion and ink jet printing ink |
US9068092B2 (en) | 2011-07-07 | 2015-06-30 | Fujifilm Imaging Colorants Limited | Process for preparing polymers, polymers, dispersions, inks and uses |
US9434808B2 (en) | 2011-07-07 | 2016-09-06 | Fujifilm Imaging Colorants Limited | Process for preparing polymers, polymers, dispersions, inks and uses |
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CN107754721A (en) * | 2017-10-12 | 2018-03-06 | 贺州学院 | Stilbene disulfonic acid natrium surfactant and its synthetic method and application |
Also Published As
Publication number | Publication date |
---|---|
DE59108367D1 (en) | 1997-01-02 |
JP3121412B2 (en) | 2000-12-25 |
KR920012058A (en) | 1992-07-25 |
EP0492501B1 (en) | 1996-11-20 |
CA2058274A1 (en) | 1992-06-22 |
EP0492501A1 (en) | 1992-07-01 |
ES2096615T3 (en) | 1997-03-16 |
DK0492501T3 (en) | 1997-04-07 |
JPH04308583A (en) | 1992-10-30 |
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